The present invention relates to new N-alkoxy-N-phenylcarbamates having microbicidal, insecticidal and acaricidal activity, a process for their preparation, new intermediates for the preparation thereof, agrochemical compositions containing these active ingredients, as well as the use thereof in the control and prevention of plant-pathogenic fungi, acarids and insects in agriculture and in the field of hygiene.
The new N-alkoxy-N-phenylcarbamates fall within formula I, 
wherein:
R1 is C1-C4-alkyl or cyclopropyl;
R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl; or C1-C6-alkyl substituted by 1 to 5 fluorine atoms;
R3 is C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C2-C6-alkinyloxy, C1-C6-alkoxycarbonyl or CN, whereby, with the exception of CN, the above-mentioned groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C1-C6-alkoxycarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, whereby the cyclic radicals in turn may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, optionally substituted benzyl, optionally substituted benzyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl and optionally substituted heteroaryloxy; whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl; or
R3 signifies aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, C1-C6-alkyl, C1-C6-alkoxy, halogen-C1-C6-alkoxy, halogen-C1-C6-alkyl, C1-C6-alkylthio, halogen-C1-C6-alkylthio, C1-C6-alkylsulfinyl, halogen-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halogen-C1-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C1-C6-alkylcarbonyl, halogen-C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, halogen-C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different, C1-C6-alkylaminothiocarbonyl, di-(C1-C6-alkyl)-aminothiocarbonyl, whereby the alkyl groups may be identical or different, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, NO2, an unsubstituted C1-C4-alkylenedioxy group or one which is mono- to tetra-substituted by C1-C4-alkyl and/or by halogen; or CN, SF5, OH and QR4;
Q signifies a direct bond, O, O(C1-C6-alkylene), (C1-C6-alkylene)O, S(xe2x95x90O)p, S(xe2x95x90O)p(C1-C6-alkylene), (C1-C6-alkylene)S(xe2x95x90O)p, C1-C8-alkylene, C2-C6-alkenylene or C2-C6-alkinylene;
R4 signifies an unsubstituted C2-C6-alkenyl- or C2-C6-alkinyl group or one which is substituted by 1 to 3 halogen atoms, a (C1-C4-alkyl)3Si group, whereby the alkyl groups may be identical or different, CN, an unsubstituted or mono- to penta-substituted C3-C6-cycloalkyl, aryl, heteroaryl or heterocyclyl group, whereby the substituents are selected from the group comprising halogen, C1-C6-alkyl, halogen-C1-C6-alkyl, C1-C6-alkoxy, halogen-C1-C6-alkoxy, phenoxy, CN, SF5, NO2, C1-C6-alkylsulfinyl, halogen-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halogen-C1-C6-alkylsulfonyl and C1-C4-alkylenedioxy, the latter being unsubstituted or mono- to tetrasubstituted by C1-C4-alkyl and/or by halogen;
p is 0, 1 or 2;
R5 signifies hydrogen or methyl;
R6 and R7 are C1-C4-alkyl;
According to the present application, formula I includes all isomeric forms and mixtures thereof, e.g. racemic mixtures and any [E/Z] mixtures. Alkylxe2x80x94as a group per se and as a structural element of other groups and compounds, such as of halogenalkyl, alkoxy and alkylthioxe2x80x94is either straight-chained, i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl.
Alkenylxe2x80x94as a group per se and as a structural element of other groups and compounds, such as of halogenalkenylxe2x80x94is either straight-chained, e.g. vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, e.g. isopropenyl.
Alkinylxe2x80x94as a group per se and as a structural element of other groups and compounds, such as of halogenalkinylxe2x80x94is either straight-chained, e.g. propargyl, 2-butinyl or 5-hexinyl, or branched, e.g. 2-ethinylpropyl or 2-propargylisopropyl.
Alkylenedioxy is xe2x80x94O(alkylene)Oxe2x80x94.
Alkylene is either straight-chained, e.g. xe2x80x94CH2CH2xe2x80x94, xe2x80x94CH2CH2CH2xe2x80x94 or xe2x80x94CH2CH2CH2CH2xe2x80x94, or branched, e.g. xe2x80x94CH(CH3)xe2x80x94, xe2x80x94CH(C2H5)xe2x80x94, xe2x80x94C(CH3)2xe2x80x94, xe2x80x94CH(CH3)CH2xe2x80x94 or xe2x80x94CH(CH3)CH(CH3)xe2x80x94.
Alkenylene is either straight-chained, e.g. vin-1,2-ylene, all-1,3-ylene, but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched, e.g. 1-methylvin-1,2-ylene.
Alkinylene is either straight-chained, e.g. propargylene, 2-butinylene or 5-hexinylene, or branched, e.g. 2-ethinylpropylene or 2-propargylisopropylene.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Halogenalkyl may contain identical or different halogen atoms.
Aryl signifies phenyl or naphthyl, preferably phenyl.
Heteroaryl signifies a cyclic aromatic group with 5 to 9 ring members in one or two rings, of which 1 to 3 members are hetero atoms selected from the group oxygen, sulphur and nitrogen. 1 to 2 benzene rings may be condensed on the heterocycle, the binding to the residual molecule taking place either through the hetero or the benzene moiety.
Examples are benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocumarinyl, benzofuryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxdiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, furyl, imidazolyl, indazolyl, indolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, ethylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, pudnyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazolo[3,4-b]pyridyl, pyridyl, pyrimidinyl, pyrrolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl and triazolyl.
Preference is given to pyridyl, pyrazinyl, pyrimidinyl, thiazolyl, quinolinyl and thienyl.
Heterocyclyl signifies a 5- to 7-membered, non-aromatic ring with one to three hetero atoms selected from the group comprising N, O and S. Preference is given to non-aromatic 5- and 6-rings that have one nitrogen atom as a hetero atom and optionally one further hetero atom.
Preference is given to pyrazolinyl, thiazolinyl and oxazolinyl.
Of the compounds of formula I, those groups are preferred, wherein:
(1)
a) R1 is methyl, ethyl or cyclopropyl, preferably methyl; or
b) R2 is methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl; or
c) R3 is C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy or C1-C6-alkoxycarbonyl, whereby the above-mentioned groups may be partially or wholly halogenated; furthermore CN, OCN or halogen; or
d) R3 signifies phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C1-C6-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkythio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl; or
e) R3 signifies phenyl which is substituted, preferably in 4-position, by QR4, wherein Q is a direct bond, O, OCH2, CH2O, S, CH2xe2x80x94CH2, xe2x80x94CHxe2x95x90CHxe2x80x94 or xe2x80x94Cxe2x89xa1Cxe2x80x94 and R4 signifies phenyl which is unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, C2-C4-alkinyl, C3-C4-alkinyloxy, C1-C4-alkoxycarbonyl or CN; or
f) R3 signifies pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkylcarbonyl, C1-C4-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, optionally substituted arylcarbonyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, or C2-C6-alkenyl; or
g) R5 signifies hydrogen, or
h) R6 and R7 signify methyl or ethyl, preferably methyl.
(2) Compounds of formula I, wherein:
R1 is methyl or ethyl, preferably methyl;
R2 signifies methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl;
R3 signifies C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy or C1-C6-alkoxycarbonyl, whereby the above-mentioned groups may be partly or wholly halogenated; furthermore CN, OCN or halogen; or
phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C1-C6-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl; or pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkylcarbonyl, C1-C4-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, optionally substituted arylcarbonyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, or C2-C6-alkenyl; and
R6 and R7 signify methyl or ethyl, preferably methyl.
(2a) Of those mentioned under (2), especially those in which:
R3 signifies phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C1-C6-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl or optionally substituted phenoxy, whereby the above-mentioned aromatic groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl.
(3) Compounds of formula I, wherein:
R1 is methyl or ethyl, preferably methyl;
R2 is C1-C6-alkyl or C1-C6-alkyl substituted by 1 to -5 fluorine atoms;
R3 is C1-C6alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl, aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby, with the exception of CN, the above-mentioned groups may be substituted as mentioned above;
R6 and R7 are methyl or ethyl, preferably methyl.
(3a) Of those mentioned under (3), especially those in which:
R2 is C1-C6-alkyl, fluoromethyl, difluoromethyl or 2,2,2-trifluoroethyl;
R3 is C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl, phenyl which is unsubstituted or mono- to tni-substituted by identical or different substituents from halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, CN, OCN, benzyl, phenyl, or phenyloxy, wherein these aromatic groups are unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C1-C2-alkyl, C1-C2-halogenalkyl or C1-C2-alkoxy.
(3b) Of those mentioned under (3a), especially those in which:
R3 is C1-C4-alkyl, C1-C4-alkoxy, C1-C6-alkoxycarbonyl, or phenyl which is unsubstituted or mono- to disubstituted by halogen, C1-C2-alkyl, C1-C2-halogenalkyl or C1-C2-alkoxy.
(4) Compounds of formula I, wherein:
R1 is methyl, ethyl or cyclopropyl, preferably methyl;
R2 is C1-C6-alkyl, preferably methyl or ethyl;
R3 is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl, aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the hydrocarbon radicals and the cyclic radicals may be substituted as mentioned above;
(4a) Of those mentioned under (4), especially those in which:
R3 is C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl.
(4b) Of those mentioned under (4), especially those in which:
R3 is phenyl which is unsubstituted or mono- or disubstituted by halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, benzyl, phenyl, or phenyloxy, wherein these aromatic groups are unsubstituted or mono- or disubstituted by halogen, C1-C2-alkyl, C1-C2-halogenalkyl or C1-C2-alkoxy.
(5) Compounds of formula I, wherein:
R1 signifies methyl, ethyl or cyclopropyl;
R2 signifies C1-C6-alkyl, preferably methyl or ethyl, C2-C6-alkenyl, preferably allyl or C2-C6-alkinyl, preferably propargyl.
R3 signifies phenyl which may be substituted by one or more identical or different substituents selected from the group comprising halogen, C1-C6-alkyl, C1-C6-alkoxy, halogen-C1-C6-alkoxy, halogen-C1-C6-alkyl, C1-C6-alkylthio, halogen-C1-C6-alkylthio, C1-C6-alkylsulfinyl, halogen-C1-C6-alkylsulfinyl, C1-C6-alkyl-sulfonyl, halogen-C1-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C3-C6-alkinyloxy, C1-C6-alkylcarbonyl, halogen-C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, halogen-C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different, C1-C6-alkylaminothiocarbonyl, di-(C1-C6-alkyl)-aminothiocarbonyl, whereby the alkyl groups may be identical or different, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, NO2, an unsubstituted C1-C4-alkylenedioxy group or one which is mono- to tetra-substituted by C1-C4-alkyl and/or by halogen; or CN, SF5, OH and QR4;
Q signifies a direct bond, O, O(C1-C6-alkylene), (C1-C6-alkylene)O, C1-C8-alkylene, C2-C6-alkenylene or C2-C6-alkinylene;
R4 signifies an unsubstituted or mono- to penta-substituted C3-C6-cycloalkyl, aryl, heteroaryl or heterocyclyl group, whereby the substituents are selected from the group comprising halogen, C1-C6-alkyl, halogen-C1-C6-alkyl, C1-C6-alkoxy, halogen-C1-C6-alkoxy, phenoxy, CN, SF5, NO2, C1-C6-alkylsulfinyl, halogen-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halogen-C1-C6-alkylsulfonyl and an unsubstituted C1-C4-alkylenedioxy or one that is mono- to tetra-substituted by C1-C4-alkyl and/or by halogen.
(5a) Of those mentioned under (5), especially those in which:
R3 signifies phenyl which is substituted, preferably in 4-position, by QR4, wherein Q is a direct bond, O, OCH2, CH2O, S, CH2xe2x80x94CH2, xe2x80x94CHxe2x95x90CHxe2x80x94 or xe2x80x94Cxe2x89xa1Cxe2x80x94 and
R4 signifies phenyl which is unsubstituted or mono- or disubstituted by identical or different substituents from halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, C2-C4-alkinyl, C3-C4-alkinyloxy, C1-C4-alkoxycarbonyl or CN.
Compounds of formula I may be produced as follows:
A) A compound of formula I is produced whereby a hydrazone of the general formula II 
wherein R1, R2 and R3 have the significances given for formula I, is reacted with an aldehyde or a ketone of the general formula III or with one of its acetal or imino derivatives of the general formulae IVa and IVb 
wherein R8 signifies optionally substituted C1-C6-alkyl or the two R8, together with the two oxygen atoms and the carbon to which they are bonded, signify a cyclic acetal.
The compounds of the general formulae II and III are known from literature (e.g. Ablov et al., Russ.J.Inorg.Chem. (Engl.Transl.), 11, 1966, 39,40; Barton, Derek H. R.; Bashiardes, George; Fourrey, Jan-Louis, Tetrahedron, 44, 1, 1988, 147-162; WO 93/15046) or may be produced by methods known per se. The compounds of the general formulae IVa and IVb may be obtained analogously to the methods described under B) and C) or directly from the carbonyl derivatives of formula III.
B) A compound of formula I is produced whereby a N-hydroxycarbamate of the general formula V, 
wherein R1xe2x80x94R3, R5 and R6 are defined as for formula I, is etherified. The compounds of the general formula V are novel and may be produced whereby
a) a N-hydroxyaniline of the general formula VI 
wherein R1xe2x80x94R3 and R5 have the significances given for formula I, is reacted with a chloroformic acid ester of the general formula VII
Clxe2x80x94COOR6xe2x80x83xe2x80x83VII
xe2x80x83or
b) a carbonyl compound of the general formula VIII 
wherein R5 and R6 have the significances given for formula I, or one of its acetal or imino derivatives VIIIa or VIIIb, is condensed with a hydrazone of the general formula II.
The compounds of formula VI are novel and may be produced by one of the following methods:
aa) a hydrazone of the general formula II is condensed with an aldehyde or ketone of the general formula IX or with one of its acetal or imino derivatives IXa or IXb 
wherein R5 is defined as for formula I and R8 is defined as for formula IV. The compounds of formula IX are known (e.g. Bamberger, Elger; Chem. Ber. 36, 3653 (1903); Fijalek, Z.; Zuman, P.; Electroanalysis 5, 53 (1993); Barth, A.; et al.; J.Am. Chem Soc. 119, 4149 (1997); Karakus C.; Zuman, P.; J.Electronanal. Chem. 396, 499 (1995)) and the acetal and imino derivatives thereof may be produced by methods known per se.
ab) a hydrazone of the general formula X 
wherein R5 signifies hydrogen or methyl, is condensed with a ketone of formula XI 
wherein R1 to R3 are as defined under formula I.
The compounds of formulae X and XI are known (e.g. Buhlmann; Einhorn; Chem. Ber. 34, 3791 (1901)) or may be produced by methods known per se.
ac) A nitro compound of the general formula XII 
wherein R1xe2x80x94R3 and R5 are as defined under formula I, is reduced analogously to the methods indicated for the preparation of compounds of formula IX. The compounds of formula XII are novel and may be obtained e.g. by condensation of the corresponding nitrocarbonyl derivatives with hydrazones of formula II.
The compounds of formula VIII are novel and may be prepared by reacting a hydroxyaniline of formula IX with a chloroformic acid ester of formula VII.
C) A compound of formula I is produced whereby an alkoxyaniline of the general formula XIII 
wherein R1xe2x80x94R3, R5 and R7 are defined as for formula I, is reacted with a chloroformic acid ester of the general formula VII.
The compounds of formula XIII are novel and may be produced by one of the following methods:
a) A hydrazone of formula II is condensed with an aldehyde or ketone of the general formula XIV or with one of its acetal or imino derivatives 
wherein R5 and R7 are defined as for formula I and R8 is defined as for formula IV.
The compounds of formulae XIV, XVa and XVb are novel and may be prepared by etherification of the N-hydroxy derivatives of formula IX.
b) A ketone of formula XI is condensed with a hydrazone of the general formula XVI 
wherein R5 and R7 are as defined under formula I. The compounds of formulae XVI are novel and may be prepared by etherificafion of the N-hydroxy derivatives of formula X.
D) A compound of formula I is produced whereby an oxime of the general formula XVII 
wherein R1, R3, and R5 to R7 are defined as for formula I, is etherified.
The compounds of formula XVII are novel and may be obtained whereby
a) a ketone of the general formula XVIII 
wherein R1, R3 and R5xe2x80x94R7 have the significances given for formula I, is reacted with hydroxylamine or with one of its salts, or
b) a compound of the general formula XIX, 
wherein R1, R3 and R5xe2x80x94R7 are defined as for formula I, is reacted with nitrous acid or with an alkyl nitrite in the presence of an acid or base, or
c) a hydrazone of the general formula XX 
wherein R1 and R3 are defined as for formula I, is reacted with an aldehyde or ketone of the general formula III or with an acetal or imine of the general formulae IVa or IVb, as a described under A).
The compounds of formulae XVIII and XIX are novel and may be obtained analogously to the preparation of the compounds of formula I.
The compounds of formula XX are known (e.g. Barany et al., J.Chem.Soc., 1951, 1929; Neber; Hartung; Ruopp, Chem.Ber., 58, 1925, 1240; Gnichtel, Horst; Toepper, Bernhard, Liebigs Ann.Chem., GE, 1989, 1071-1074; Rapoport,H.; Nilsson,W., J.Amer.Chem.Soc., 83, 1961, 4262-4267).
E) A compound of formula I may be produced whereby a ketone of the general formula XVIII is reacted with an alkoxyamine of the general formula XXI
R2xe2x80x94ONH2xe2x80x83xe2x80x83XXI
wherein R2 is defined as for formula I, or with one of its salts.
All the above-described reactions are known per se. The novel, above-mentioned intermediates were developed especially for the present invention and similarly form an object of this invention. Those of formulae IV, V, VI, VIII, XII-XIX are of particular significance.
The compounds of formula I are of preventive and/or curative merit as active ingredients for the control of plant pests and may be used in the agricultural sector and related fields The active ingredients of formula I according to the invention are notable for their good activity even at low concentrations, for their good plant tolerance and for their environmental acceptability. They possess very advantageous, especially systemic properties, and may be used for the protection of numerous cultivated plants. Using the active ingredients of formula I, pests appearing on plants or plant parts (fruits, flowers, foliage, stems, tubers, roots) of different crops can be checked or destroyed, whereby parts of the plant which grow later are also protected e.g. from phytopathogenic micro-organisms.
The compounds of formula I may also be be employed as a dressing for seeds (fruits, tubers, grain) and plant cuttings to protect against fungal infections, and to protect against phytopathogenic fungi appearing in the soil.
Compounds I are effective for example against the phytopathogenic fungi belonging to the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria); Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia); Ascomycetes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e.g. Phytophthora, Pythium, Plasmopara).
Target cultivations for the plant-protecting usage in the context of the invention are, for example, the following species of plant: cereals, (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybean); oleaginous fruits (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (squashes, cucumbers, melons); fibrous plants (cotton, flax, hemp or jute); citrus fruits (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); Lauraceae (avocado, cinnamon, camphor); and plants such as tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, banana plants, natural rubber plants and ornamental.
In addition, the compounds of formula I according to the invention are valuable active ingredients against insects and pests of the order Acarina, such as those appearing on crop plants and ornamentals in agriculture and horticulture and in forestry, whilst being tolerated well by warm-blooded animals, fish and plants. The compounds of formula I are especially suitable for controlling pests in cultivations of cotton, vegetables, fruit and rice, such as spider mites, aphids, caterpillars and plant and leaf hoppers in rice. The pests which are primarily controlled are spider mites such as Panonychus ulmi, aphids such as Aphis craccivora, caterpillars such as those of Heliothis virescens and plant and leaf hoppers in rice, such as Nilaparvata lugens or Nephotettix cincticeps. 
The good pesticidal activity of the compounds I according to the invention corresponds to a mortality rate of at least 50-60% of the pests mentioned.
Further fields of application for the active ingredients according to the invention are the protection of stock and material, where the goods stored are protected against rotting and mildew, as well as against animal pests (e.g. grain weevils, mites, maggots, etc). In the hygiene sector, compounds of formula I provide successful control of animal parasites such as ticks, mites, warble flies etc., on domestic animals and productive livestock Compounds I are effective against individual or all stages of development of pests showing normal sensitivity, and also of those showing resistance Their activity may be demonstrated, for example, by the mortality of the pests, which occurs immediately or only after some time, for example during a moult, or by reduced egg laying and/or hatching rate.
Compounds I are used in this instance in unmodified form or preferably together with the excipients that are usual in formulation technology. To this end, they are suitably processed in known manner e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts or granules, e.g. by encapsulation in e.g. polymeric substances. As with the type of compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.
Suitable carriers and additives may be solid or liquid and are substances that are appropriate in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binding agents or fertilisers.
The compounds of formula I may be mixed with further active ingredients, e.g. fertilisers, trace element intermediates or other plant-protecting compositions, especially with further fungicides. Unexpected synergistic effects may thus occur.
Preferred mixture components are:
azoles, such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, tritconazole; pynmidinyl carbinols, such as ancymidol, fenarimol, nuarimol; 2-amino-pyrimidines, such as bupinmate, dimethirimol, ethirimol; morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph; anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil; pyrroles, such as fenpiclonil, fludioxonil; phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl; benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole; dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozolin; carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine;
strobilurines, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, CGA 279202 (trifloxystrobin); dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram; N-halogenmethylthiophthalimides, such as captafol, captan, dichlofluanid, fluoromide, folpet, tolyfluanid; Cu compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper; nitrophenol derivatives, such as dinocap, nitrothal-isopropyl; organo-P derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen,. pyrazophos, tolclofos-methyl; various, such as AC 382042, acibenzolar-S-methyl, anilazine, blasticidin-S, quinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etridiazole, famoxadone, fenamidone, fenhexamid, fentin, ferimzone, fluazinam, flusulfamide, fosetyl-aluminium, hymexazol, IKF-916, iprovalicarb, kasugamycin, methasulfocarb, MON65500, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, RH-7281, RPA 407213, sulfur, triazoxide, tricyclazole, triforine, validamycin.
One preferred method of applying an active ingredient of formula I or an agrochemical composition containing at least one of these active ingredients is application to the foliage (leaf application). The frequency and rate of application depend on the severity of infestation by the invader in question. However, the active ingredients I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plants with a liquid preparation, or by applying the substances to the soil in solid form, for example in granular form (soil application). With paddy rice cultures, granules may be metered into the flooded paddy field. The compounds I may also be applied to seed grain for seed pre-treatment (coating) by either drenching the grains or tubers in a liquid preparation of the active ingredient or coating them with a solid preparation. The compositions are prepared in known manner, e.g. by intimately mixing and/or grinding the active ingredient with extenders, such as solvents, solid carriers and optionally surface-active compounds (surfactants).
The agrochemical compositions normally contain 0.1 to 99 percent by weight, especially 0.1 to 95 percent by weight, of active ingredient of formula 1, 99.9 to 1 percent by weight, especially 99.8 to 5 percent by weight, of a solid or liquid additive and 0 to 25 percent by weight, especially 0.1 to 25 percent by weight, of a surfactant.
Favourable application rates generally lie between 1 g and 2 kg of active substance (AS) per hectare (ha), preferably between 10 g and 1 kg AS/ha, especially between 20 g and 600 g AS/ha.
For usage as a seed dressing, the dosages advantageously used are 10 mg to 1 g of active substance per kg seeds.
Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
The compositions may also contain further additives, such as stabilisers, anti4oaming agents, viscosity regulators, binding agents or tackifiers, as well as fertilisers or other active ingredients, in order to achieve special effects.

A solution of 27.4 g of (2-bromomethyl-phenyl)-N-methoxycarbamic acid methyl ester in 50 ml of acetonitrile is added dropwise at room temperature to 40 g of N-methyl-morpholine-N-oxide in 150 ml of acetonitrile. After stirring for 16 hours, the mixture is concentrated and the residue partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate and, after drying over sodium sulphate, the solvent is distilled from the combined organic phases. The residue is purified on silica gel using ethyl acetate/hexane (1:5% by volume). The title compound is obtained in the form of a yellow oil.

A solution of 1.05 g of (2-formyl-phenyl)-N-methoxycarbamic acid methyl ester and 1.05 g of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime in 5 ml of methanol is stirred at room temperature for 4 hours. The resulting by-product (symmetric azine of 1-(4-fluorophenyl)-2-hydrazono-propan-1-on-O-methyl-oxime) is removed by filtration and the filtrate is placed in a refrigerator over night. The product which has crystallised is filtered off (1.0 g). By concentrating the mother liquor and by means of fractional crystallisation of the residue, a further 0.48 g of the title compound are obtained in the form of yellow crystals having a melting point of 88-90xc2x0 C.
The compounds of the following tables may be produced in analogous manner. Abbreviations: i: iso; s: sec; t: tert
Table 1
Compounds of the general formula I.1, in which R2, R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A. 
Table 2
Compounds of the general formula I.1, in which R2 signifies ethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 3
Compounds of the general formula I.1, in which R2 signifies difluoromethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 4
Compounds of the general formula I.1, in which R2 signifies 2,2,2-trifluoroethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 5
Compounds of the general formula I.1, in which R2 and R6 signify methyl and R7 signifies ethyl and R3 corresponds in each case to one line of Table A.
Table 6
Compounds of the general formula I.1, in which R2 and R7 signify ethyl and R6 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 7
Compounds of the general formula I.1, in which R2 and R6 signify ethyl and R7 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 8
Compounds of the general formula I.1, in which R2 signifies methyl and R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 9
Compounds of the general formula I.1, in which R2, R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 10
Compounds of the general formula I.1, in which R2 signifies n-propyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 11
Compounds of the general formula I.2, in which R2, R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A. 
Table 12
Compounds of the general formula I.2, in which R2 signifies ethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 13
Compounds of the general formula I.2, in which R2 signifies difluoromethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 14
Compounds of the general formula I.2, in which R2 signifies 2,2,2-trifluoroethyl and R8 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 15
Compounds of the general formula I.2, in which R2 and R6 signify methyl and R7 signifies ethyl and R3 corresponds in each case to one line of Table A.
Table 16
Compounds of the general formula I.2, in which R2 and R7 signify ethyl and R6 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 17
Compounds of the general formula I.2, in which R2 and R6 signify ethyl and R7 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 18
Compounds of the general formula I.2, in which R2 signifies methyl and R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 19
Compounds of the general formula I.2, in which R2, R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 20
Compounds of the general formula I.2, in which R2 signifies n-propyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 21
Compounds of the general formula I.3, in which R2, R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A. 
Table 22
Compounds of the general formula I.3, in which R2 signifies ethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 23
Compounds of the general formula I.3, in which R2 signifies difluoromethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 24
Compounds of the general formula I.3, in which R2 signifies 2,2,2-trifluoroethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 25
Compounds of the general formula I.3, in which R2 and R6 signify methyl and R7 signifies ethyl and R3 corresponds in each case to one line of Table A.
Table 26
Compounds of the general formula I.3, in which R2 and R7 signify ethyl and R6 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 27
Compounds of the general formula I.3, in which R2 and R6 signify ethyl and R7 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 28
Compounds of the general formula I.3, in which R2 signifies methyl and R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 29
Compounds of the general formula I.3, in which R2, R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 30
Compounds of the general formula I.3, in which R2 signifies n-propyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 31
Compounds of the general formula I.4, in which R2, R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A. 
Table 32
Compounds of the general formula I.4, in which R2 signifies ethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 33
Compounds of the general formula I.4, in which R2 signifies difluoromethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 34
Compounds of the general formula I.4, in which R2 signifies 2,2,2-trifluoroethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 35
Compounds of the general formula I.4, in which R2 and R6 signify methyl and R7 signifies ethyl and R3 corresponds in each case to one line of Table A.
Table 36
Compounds of the general formula I.4, in which R2 and R7 signify ethyl and R6 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 37
Compounds of the general formula I.4, in which R2 and R6 signify ethyl and R7 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 38
Compounds of the general formula I.4, in which R2 signifies methyl and R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 39
Compounds of the general formula I.4, in which R2, R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 40
Compounds of the general formula I.4, in which R2 signifies n-propyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 41
Compounds of the general formula I.5, in which R2, R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A. 
Table 42
Compounds of the general formula I.5, in which R2 signifies ethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 43
Compounds of the general formula I.5, in which R2 signifies difluoromethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 44
Compounds of the general formula I.5, in which R2 signifies 2,2,2-trifluoroethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 45
Compounds of the general formula I.5, in which R2 and R6 signify methyl and R7 signifies ethyl and R3 corresponds in each case to one line of Table A.
Table 46
Compounds of the general formula I.5, in which R2 and R7 signify ethyl and R6 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 47
Compounds of the general formula I.5, in which R2 and R6 signify ethyl and R7 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 48
Compounds of the general formula I.5, in which R2 signifies methyl and R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 49
Compounds of the general formula I.5, in which R2, R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 50
Compounds of the general formula I.5, in which R2 signifies n-propyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 51
Compounds of the general formula I.6, in which R2, R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A. 
Table 52
Compounds of the general formula I.6, in which R2 signifies ethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 53
Compounds of the general formula I.6, in which R2 signifies difluoromethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 54
Compounds of the general formula I.6, in which R2 signifies 2,2,2-trifluoroethyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 55
Compounds of the general formula I.6, in which R2 and R6 signify methyl and R7 signifies ethyl and R3 corresponds in each case to one line of Table A.
Table 56
Compounds of the general formula I.6, in which R2 and R7 signify ethyl and R6 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 57
Compounds of the general formula I.6, in which R2 and R6 signify ethyl and R7 signifies methyl and R3 corresponds in each case to one line of Table A.
Table 58
Compounds of the general formula I.6, in which R2 signifies methyl and R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 59
Compounds of the general formula I.6, in which R2, R6 and R7 signify ethyl and R3 corresponds in each case to one line of Table A.
Table 60
Compounds of the general formula I.6, in which R2 signifies n-propyl and R6 and R7 signify methyl and R3 corresponds in each case to one line of Table A.
Table 62
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies OCH2 and Z corresponds in each case to one line of Table B.
Table 63
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies CH2O and Z corresponds in each case to one line of Table B.
Table 64
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies S and Z corresponds in each case to one line of Table B.
Table 65
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies xe2x80x94Cxe2x89xa1Cxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 66
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies xe2x80x94CHxe2x95x90CHxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 67
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies xe2x80x94CH2xe2x80x94CH2xe2x80x94 and Z corresponds in each case to one line of Table B.
Table 68
Compounds of the general formula I.7, wherein R5 signifies H, R1 and R2 signify methyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.
Table 69
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 70
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies OCH2 and Z corresponds in each case to one line of Table B.
Table 71
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies CH2O and Z corresponds in each case to one line of Table B.
Table 72
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies S and Z corresponds in each case to one line of Table B.
Table 73
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies xe2x80x94Cxe2x89xa1Cxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 74
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies xe2x80x94CHxe2x95x90CHxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 75
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies xe2x80x94CH2xe2x80x94CH2xe2x80x94 and Z corresponds in each case to one line of Table B.
Table 76
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies ethyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.
Table 77
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 78
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies OCH2 and Z corresponds in each case to one line of Table B.
Table 79
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies CH2O and Z corresponds in each case to one line of Table B.
Table 80
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies S and Z corresponds in each case to one line of Table B.
Table 81
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies xe2x80x94Cxe2x89xa1Cxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 82
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies xe2x80x94CHxe2x95x90CHxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 83
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies xe2x80x94CH2xe2x80x94CH2xe2x80x94 and Z corresponds in each case to one line of Table B.
Table 84
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies methyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.
Table 85
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 86
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies OCH2 and Z corresponds in each case to one line of Table B.
Table 87
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies CH2O and Z corresponds in each case to one line of Table B.
Table 88
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies S and Z corresponds in each case to one line of Table B.
Table 89
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies xe2x80x94Cxe2x89xa1Cxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 90
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies xe2x80x94CHxe2x95x90CHxe2x80x94 and Z corresponds in each case to one line of Table B.
Table 91
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies xe2x80x94CH2xe2x80x94CH2xe2x80x94 and Z corresponds in each case to one line of Table B.
Table 92
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies ethyl, Q signifies a direct bond and Z corresponds in each case to one line of Table B.
Table 93
Compounds of the general formula I.7, wherein R5 signifies methyl, R1 and R2 signify methyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 94
Compounds of the general formula I.7, wherein R5 signifies methyl, R1 signifies ethyl and R2 signifies methyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 95
Compounds of the general formula I.7, wherein R5 signifies methyl, R1 signifies methyl and R2 signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 96
Compounds of the general formula I.7, wherein R5 signifies methyl, R1 signifies ethyl and R2 signifies ethyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 97
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies propargyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 98
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies propargyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 99
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies allyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 100
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies allyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 101
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies n-propyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 102
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies n-propyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 103
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies methyl and R2 signifies isopropyl, Q signifies O and Z corresponds in each case to one line of Table B.
Table 104
Compounds of the general formula I.7, wherein R5 signifies H, R1 signifies ethyl and R2 signifies isopropyl, Q signifies O and Z corresponds in each case to one line of Table B.
Details of the physical data in the following Tables: xc2x0=m.p. in xc2x0Celsius; Number=chemical displacement of R5 in 1H-NMR (.xcex4.in ppm); * isomers
Formulations may be prepared analogously to those described for example in WO 97/33890.
In the following patho-systems, compounds from the tables display good activity.
A. Fungicidal Activity